Triisopropyl borate mediated N -sulfinyl imine formation

Abstract Triisopropyl borate effects the condensation of aldehydes with sulfinamides to give N -sulfinyl imines. The reaction is amenable to 1°, 2°, and 3° alkyl aldehydes, as well as aryl, heteroaryl, and α,β-unsaturated aldehydes. In addition to tert -butanesulfinamide, the condensation is also effective with 4-toluenesulfinamide and 2,4,6-triisopropylphenylsulfinamide. This protocol proceeds under homogeneous reaction conditions and requires no post-reaction filtration of insoluble reagents or byproducts.